Ammonium 1,3,4,6-tetranitro-2,5-diazapentalene

Butcher, Ray J.; Bottaro, Jeffrey C.; Gilardi, Richard

doi:10.1107/s1600536803015101

Cited by 2 publications

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References 2 publications

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“…23,24 Apart from tetraphenylthieno(3,4-c)thiophene (IIe), [14][15][16] there is no experimental evidence for molecules IIb-d or their derivatives (though Closs et al reported 25 experimental evidence for II with X ) N) nor for IIIb-d, but crystal structures of potassium and ammonium salts of the dianion of 1,3,4,6tetranitro-2,5-diazapentalene have been published. 26,27 Compound VI, 7,8-diazapentalene, is the least stable diazapentalene isomer, nevertheless its derivatives were obtained and the crystal structures of nitro-substituted-7,8-diazapentalenes were reported. 28,29 The calculated structure of IId (Table 1) agrees well with the structure of IIe; the calculated ionization potential (6.35 eV, Table 3) is also in good agreement with experiment (6.19 eV 16 ).…”

Section: Discussionmentioning

confidence: 99%

Biradicals Stabilized by Intramolecular Charge Transfer: Properties of Heterosubstituted Pentalene and Cyclooctatetraene Biradicals

Zilberg

Haas

2006

J. Phys. Chem. A

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Intramolecular charge transfer can lead to substantial stabilization of singlet ground state and a corresponding increase of the singlet-triplet gap for molecules isoelectronic with the dianions of antiaromatic hydrocarbons. The formal biradicals 2,5-di-heterosubstituted-pentalenes and 1,5-di-heterosubstituted-cyclooctatetraenes are theoretically predicted to have the potential to be stable, persistent non-Kekulé molecules, as supported by high-level quantum chemical calculations. The singlet-triplet energy gaps and the S(0)-S(1) excitation energies of these molecules are similar to those of aromatic molecules rather than standard biradicals. These formal biradicals have a pronounced zwitterionic character, having a singlet ground state. The marked stabilization of the ground-state singlet for these non-Kekulé molecules is accompanied by a significant destabilization of the highest occupied molecular orbital (HOMO), leading to a low ionization potential (IP). This apparent inconsistency is explained by analyzing the electronic structure of the molecules. In the case of di-aza-pentalene, the energy of the first electronic excited state is only slightly lower than the ionization potential, making it a candidate for molecular autoionization.

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Section: Discussionmentioning

confidence: 99%

Biradicals Stabilized by Intramolecular Charge Transfer: Properties of Heterosubstituted Pentalene and Cyclooctatetraene Biradicals

Zilberg

Haas

2006

J. Phys. Chem. A

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The Nitrogen Bond, or the Nitrogen-Centered Pnictogen Bond: The Covalently Bound Nitrogen Atom in Molecular Entities and Crystals as a Pnictogen Bond Donor

Varadwaj

Marques

et al. 2022

Compounds

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The nitrogen bond in chemical systems occurs when there is evidence of a net attractive interaction between the electrophilic region associated with a covalently or coordinately bound nitrogen atom in a molecular entity and a nucleophile in another, or the same molecular entity. It is the first member of the family of pnictogen bonds formed by the first atom of the pnictogen family, Group 15, of the periodic table, and is an inter- or intra-molecular non-covalent interaction. In this featured review, we present several illustrative crystal structures deposited in the Cambridge Structure Database (CSD) and the Inorganic Crystal Structure Databases (ICSD) to demonstrate that imide nitrogen is not the only instance where nitrogen can act as an electrophilic agent. Analysis of a set of carefully chosen illustrative crystal systems shows that a covalently bound nitrogen atom in a variety of molecular entities features a σ-hole or even a π-hole, and these have the ability to sustain attractive engagements with negative sites to form inter- and/or intramolecular interactions that drive, or assist, the formation of a crystalline phase.

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Ammonium 1,3,4,6-tetranitro-2,5-diazapentalene

Cited by 2 publications

References 2 publications

Biradicals Stabilized by Intramolecular Charge Transfer: Properties of Heterosubstituted Pentalene and Cyclooctatetraene Biradicals

Biradicals Stabilized by Intramolecular Charge Transfer: Properties of Heterosubstituted Pentalene and Cyclooctatetraene Biradicals

The Nitrogen Bond, or the Nitrogen-Centered Pnictogen Bond: The Covalently Bound Nitrogen Atom in Molecular Entities and Crystals as a Pnictogen Bond Donor

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